Water → 1H-Benzimidazole-4-carbohydrazide

HRID 2180260Notes

Reaction equation

HRID 2180260 reaction equation
C[O:2][C:3]([C:5]1[C:10]2[N:11]=[CH:12][NH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.O.[NH2:15][NH2:16].O>CCO>[N:11]1[C:10]2[C:5]([C:3]([NH:15][NH2:16])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 14970852Methyl 1H-benzimidazole-4-carboxylate

Product 1

HCID 450778831H-Benzimidazole-4-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzimidazole ester 3 (1.65 g, 9.36 mmol), hydrazine monohydrate (10 mL), and water (3 mL) were refluxed in EtOH (60 mL) for 24 hs. Reaction mixture was cooled to room temperature and solid formed was filtered, washed with EtOH and dried to give 1.13 g (68%) of pure 4: 1H NMR (DMSO-d6) δ 12.31 (br.s, 1H), 10.59 (s, 1H), 8.44 (s, 1H), 7.86 (d, 1H, J=6.5 Hz), 7.76 (d, 1H, J=8.0 Hz), 7.34 (t, 1H, J=8.0 Hz), 4.68 (s, 2H).

Workup

  1. customReaction mixture
  2. customsolid formed
  3. filtrationwas filtered
  4. washwashed with EtOH
  5. customdried
  6. customto give 1.13 g (68%) of pure 4

Sources & evidence

ORD record
ord-29a7ecfe00e6434b8806fc474de3f30c
Source dataset
uspto-grants-2005_05
Patent number
US06887996B2

Reaction notes

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